N-[N-(4,6-dimethoxypyrimidin-2-yl)-N'-hydroxycarbamimidoyl]-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide | 916760-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-[N-(4,6-dimethoxypyrimidin-2-yl)-N'-hydroxycarbamimidoyl]-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide
• 英文别名: N-{[(4,6-Dimethoxypyrimidin-2-yl)amino](hydroxyamino)methylidene}-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide；1-(4,6-dimethoxypyrimidin-2-yl)-3-hydroxy-2-[2-methoxy-4-(trifluoromethyl)pyridin-3-yl]sulfonylguanidine
• CAS: 916760-02-6
• 化学式: C₁₄H₁₅F₃N₆O₆S
• 分子量: 452.371
• InChiKey: ZGMPCNCREIQHNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  166
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  光气 、 N-[N-(4,6-dimethoxypyrimidin-2-yl)-N'-hydroxycarbamimidoyl]-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide 在 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 1.67h， 生成
  参考文献：
  名称：

  Application of the Tisler Triazolopyrimidine Cyclization to the Synthesis of a Crop Protection Agent and an Intermediate

  摘要：

  A new synthetic route to the Dow AgroSciences early stage sulfonamide herbicide 3-(2-methoxy-4-trifluoromethyl)-N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)pyridinesulfonamide (pyroxsulam) has been developed. The synthesis is based on formation of the triazole ring as the final step, utilizing the Tisler triazolopyrimidine cyclization. A Tisler cyclization route to 2-amino-5,7-dimethoxy-1,2,4-trazolo[1,5-a]pyrimidine starting with 2-chloro-4,6-dimethoxypyrimidine has also been demonstrated.

  DOI：

  10.1021/op0601518
• 作为产物：
  描述：

  N-(4,6-dimethoxy-pyrimidin-2-yl)-thiourea 在 盐酸羟胺 、 sodium acetate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.5h， 生成 N-[N-(4,6-dimethoxypyrimidin-2-yl)-N'-hydroxycarbamimidoyl]-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide
  参考文献：
  名称：

  Application of the Tisler Triazolopyrimidine Cyclization to the Synthesis of a Crop Protection Agent and an Intermediate

  摘要：

  A new synthetic route to the Dow AgroSciences early stage sulfonamide herbicide 3-(2-methoxy-4-trifluoromethyl)-N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)pyridinesulfonamide (pyroxsulam) has been developed. The synthesis is based on formation of the triazole ring as the final step, utilizing the Tisler triazolopyrimidine cyclization. A Tisler cyclization route to 2-amino-5,7-dimethoxy-1,2,4-trazolo[1,5-a]pyrimidine starting with 2-chloro-4,6-dimethoxypyrimidine has also been demonstrated.

  DOI：

  10.1021/op0601518

文献信息

• Application of the Tisler Triazolopyrimidine Cyclization to the Synthesis of a Crop Protection Agent and an Intermediate
  作者：Bruce M. Bell、Phillip E. Fanwick、Paul R. Graupner、Gary A. Roth

  DOI：10.1021/op0601518

  日期：2006.11.1

  A new synthetic route to the Dow AgroSciences early stage sulfonamide herbicide 3-(2-methoxy-4-trifluoromethyl)-N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)pyridinesulfonamide (pyroxsulam) has been developed. The synthesis is based on formation of the triazole ring as the final step, utilizing the Tisler triazolopyrimidine cyclization. A Tisler cyclization route to 2-amino-5,7-dimethoxy-1,2,4-trazolo[1,5-a]pyrimidine starting with 2-chloro-4,6-dimethoxypyrimidine has also been demonstrated.